


Wednesday

by Sincestiel



Series: One Week [1]
Category: Supernatural
Genre: Alternate Universe - Prostitution, Destiel - Freeform, Dirty Talk, Hooker AU, Jock Strap, M/M, Prostitute Dean, Prostitution, Toys, cliched falling for the client sort of thing, slight D/s
Language: English
Status: Completed
Published: 2013-11-05
Updated: 2013-11-05
Packaged: 2017-12-31 13:34:59
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,935
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1032291
Author URL: https://archiveofourown.org/users/Sincestiel/pseuds/Sincestiel
Summary: <blockquote class="userstuff">
              <p>Dean's favorite day of the week is Wednesday.  Wednesday is the only thing that gets him through every other day of his life.  Wednesday means Castiel.</p>
            </blockquote>





	Wednesday

Dean's favorite day of the week is Wednesday. Wednesday is the only thing that gets him through every other day of his life. Wednesday means Castiel.

Cas is spread out on his bed, arms and legs splayed wide. He's naked except for the jock strap that frames his pert cheeks. And Dean finds the sight more than a little arousing.

He's already squirming a little, anticipation getting the best of him, as Dean surveys the toys Cas has laid out for him today. Only two. One long black wand with a rubber handle ribbed for a better grip or a more interesting sensation if it's turned around. And one short, pink, crooked vibrator, perfect to hit his sweet spot. A bottle of KY sits beside a wad of cash that Dean pockets without counting – because Cas has never shorted him. And then they're ready to get started.

Dean doesn't bother with getting undressed, knows Castiel likes it like this. He gets off on the feel of Dean's jeans rubbing his thighs. Likes knowing he's on display for Dean. 

Castiel lets a small moan escape when Dean climbs onto the bed, lube in one hand and the toys in the other. He nudges Castiel's legs upward and is rewarded with the sight of Castiel's pretty little hole when the motion pulls his cheeks apart.

God, he's gorgeous like this. And Dean knows he sometimes thinks of Cas in ways he shouldn't think of a client. But he can't help himself. Cas makes it so easy to fall down that rabbit hole with his big, pretty blue eyes and his plump lips and the way he begs all sweetly for Dean. He's also a virgin. Well, when it comes to actual penetrative sex with another person anyway. It isn't like he's never been stuffed full. Dean does that for him on a regular basis.

It's also hard to see Castiel as just another client because of what he asks of Dean. He doesn't want Dean's submission, like so many (all) of his other clients do. No. Castiel wants to offer his to Dean. When their hour starts, Dean is in full control. Oh, there are rules, of course. Castiel is adamant that he does not want to be penetrated with anything other than fingers or toys. He doesn't touch Dean and Dean keeps his touches centered on Cas' thighs, lower back, and ass. 

But Dean can work with that. He does every week. And leaves Castiel happy and sated. Plus, it's easier to stick to the rules when he knows he's going to be allowed to get off too. Maybe it's not the way he'd really like, but it's better than nothing. Which is what he generally gets from the closeted assholes he usually sees. 

He thinks, if he asked nicely enough, Cas might suck his cock for him. But it would be just that, Cas doing it for him and not because it's something he wants or has paid for (and who is Dean kidding? No one pays to suck cock, or at least not that he knows of). So Dean doesn't push it. Also, he may be a bit of a girl, because there's this little part of him that doesn't want to take any of Cas' firsts. Cas deserves to have that be with someone he loves. Not a whore like Dean.

So the rules are important. And really, if this is all Dean ever gets of Castiel, he can live with it. Because at least he gets this. And as far as he knows, he's the only person who's ever seen Cas like this, desperate and needy, rutting against the mattress before he's even been touched. It's nice.

"So hot, baby," Dean says as he pops the top on the lube and lets a few drops fall on his fingers.

Castiel doesn't reply, rarely talks until he's on the edge of orgasm, but the little whimper that comes from him is encouragement enough for Dean to keep going.

Resting the bottle of lube against the inside of his thigh to make sure it doesn't topple and spill, Dean slips his slick fingers up the crack of Cas' ass. The lube is still cool, and Castiel starts but then relaxes into it. And Dean wastes no time in sliding one finger halfway into the tight clench of Castiel's body.

Cas groans and tries to pull his legs up, spread himself even more, like he's just been dying for this. Like he's been anxiously waiting since last week just to be right here again, with Dean fingering him open.

"That's it, sweetheart, gonna take it all for me? You need to if you want this dildo inside you. Gonna fuck you so good with it. Just open up for me."

The terms of endearment fall so easily from his lips with Cas, where, on rare occasions when he uses them with other clients, they feel forced and wrong. But nothing Dean says to Cas is contrived. He means every word. And while that is a little worrisome, Dean just pushes it to the back of his mind. He's examined this thing with Castiel enough in the past to fully understand it. Even if he doesn't like to think about it.

Castiel swallows his finger easily enough and soon he's taking two, keening and arching his back. So pretty all stretched around Dean's fingers. Dean wishes he could taste him. Lube and all. Just lean down and lick a stripe up Castiel's crack, delve into his hole. Open him like that, with fingers and lips and tongue until Castiel is coming all over himself. But Dean refrains. They've never discussed that and he doesn't want to overstep his bounds.

"So hungry for me, aren't you? God, Cas, if you could see yourself. Just opening up and taking my fingers like a little slut."

Castiel releases a stuttered breath at that, and Dean grins wolfishly. He knows just what buttons to press with Cas. Filthy sweet is how he likes it. Castiel doesn't want to be degraded or humiliated. But he likes that edge. Like it _could_ turn into that. Like Dean could suddenly use him and abuse him and drag out all of his dirtiest fantasies only to shame him for them. Like he could but he won't. Almost but not quite lewd to the point of rudeness. And Dean likes it just as much as Cas does.

Dean always gets so hard for Cas. But when Castiel is taking both fingers and starting to mutter that he needs more, Dean manages to pull out of his very realistic daydream of fucking Cas face to face – those blue eyes boring into his as he pushes Castiel over the edge with nothing but his cock – and let his fingers be pushed out of Castiel's slightly puffy hole. 

"Want more, don't you, Cas? Need it deep and hard, baby? Want this big, long dildo up your ass? Gonna imagine it's my cock?"

Castiel shivers from head to toe and Dean just barely catches Castiel's little nod. But god, that's… Dean wants to offer to give it to him. To take him bare, just like this, and make him come so fucking hard. Give him the real thing so good that he never wants anything but Dean's cock ever again.

Quickly Dean rubs a bit more lube into Cas' hole and then slicks up the toy. Once he's satisfied, he tosses the bottle aside, no longer caring if it spills. He needs to get something inside Cas right now.

Dean leans up, putting his mouth close to Cas' ear as he grips the rubber handle and positions the long toy at Castiel's entrance. Breathing one warm breath over Castiel's skin and then sliding just the tip in, Dean whispers, "You could have it, you know. I could take my cock out, just through the opening in my jeans, pull you up to your knees, and slide right in. Have you all naked and wet and warm, writhing around on my dick. I could do it, Cas. Grab your hips and pull you back on me, make you take it all and love it."

As he says the last few words, he pumps his hand once, filling Cas more than he's experienced in a week, before pulling back so that just the tip is resting inside his rim. Castiel jerks for him, whether at Dean's words or at the sudden intrusion, Dean isn't sure. Maybe a combination of both. But it gives Dean an idea. An idea that skirts almost but not quite outside the rules.

"What do you say, Cas? Want me to use this," he twirls the stick, letting it sink a little deeper, "And show you how it would feel to be fucked like that?"

This time, Castiel's nod is obvious and followed by an affirmative grunt, like he can't even get the words out. But Dean doesn't make him, knows that soon enough Castiel will be openly begging him, no traces of sheepishness to be found.

Lifting up again, Dean pushes the toy in far enough that it won't slip out and admires the way it wags around a bit as he pulls Cas up to his hands and knees. And this is a new position, because Cas usually ruts himself to orgasm against the bed. But Dean's sudden desire to make him come like this, with nothing to press against for friction, has him ordering Cas to stay put.

"Just like this, Castiel. This is how you come today, understand?"

Cas squeaks out a panting, "Yes, please," and then bows his head, letting it hang between his arms. 

For a moment, Dean makes him stay just like that: black wand dangling from his ass as it tries and fails to submit to gravity, legs spread as wide as they can go in this position, and his hips thrusting back in tiny increments, wanting desperately.

Finally, when he's heard Castiel whine for the fifth time, he braces himself with one hand on Cas' hip and the other around the base of the toy. Obviously he's going to have to be more careful than he would if it was his cock, but the motion is the same.

So he starts slow, hitches of his hips that guide the toy deeper, and then holding it steady with his hand as he pulls out. And Cas quakes with each movement, fingers digging into the sheets as sweat builds at the bottom of his spine. Dean can count every knob on it as Castiel arches and bows for him, accommodating his rhythm perfectly.

Out of all the times he's watched this man fall apart for him, this is, by far, the hottest. And Dean himself is heaving for air much quicker than normal. His cock is thick and heavy in his jeans, only getting the barest hint of friction from the toy rubbing against him as he presses in. And God, does he really want to press in. Get the barriers out of the way and fuck Cas hard and deep and slow, just the way Cas likes.

"Look so good like this, sweetheart. Want you so much, Cas. God," And he did not mean to say that, but the response it elicits from Cas is interesting, to say the least. Because he doesn't shy away at all. If anything, he pushes back harder, and the sound he makes goes straight to Dean's cock, forcing out another dribble of pre-come into his underwear.

"Yeah. Want… yeah. Dean… Please," it's almost permission. But Castiel is high on sex right now, wrung out and close to coming. And Dean cannot take that as acquiescence, as much as he'd like to.

"One of these days, baby. When you're ready," He almost adds, _when you're not paying me_ , but closes his lips tight around those words. Refuses to let them out.

He leaves it at that, turns his focus to Castiel's ass, the way his pale cheeks look being split open by the end of the toy as it dips into his body, the way his reddened hole clings to the plastic as he pulls it out. Tighter, Dean thinks, it would cling even tighter to flesh. At that thought, he lets out a moan of his own to join the ones falling continuously from Castiel's mouth.

And that's it, he has to get a hand on himself. Right now. And he needs Cas to come soon, because he won't until Castiel has. 

Cas whimpers and wriggles around invitingly when Dean pulls the length of the black toy from his hole. It gapes a bit, like it wasn't quite ready to give up the intruder. But Dean doesn't leave Cas hanging for long. He fumbles around for the little pink vibrator and the – thankfully still full – bottle of lube.

In seconds he's sliding it into Castiel's waiting body, moving closer and unzipping his pants with one hand. And then his dick is out and the flicks the toy on as he lets his tip just brush the back of Cas' thigh.

And Cas jerks toward his cock, over and down, like he instinctively knows it's exactly what he needs. Like his body is trying to make a decision without help from his brain. Dean pants out, fingernails biting into Cas' hip as he fights the urge to pull the toy out and slide home. Instead, he leans over Cas' back, presses a kiss to his overheated skin.

"Come on, baby. Need you to come for me. So ready. Wanna dirty up your little hole, sweetheart. Come all over it."

That gets Cas begging, brokenly and almost incoherently. Dean makes out only certain words. But what he hears is enough to push him even closer. Cas begging Dean to come on him. God, to come _in_ him, if Dean's hearing it right. But he just rests his forehead on Cas' back, pushing and pulling with the toy, hitting Cas' prostate head on judging by the way he's whimpering gibberish and biting at his own arm to hold in the sounds.

Suddenly, Cas goes completely still, letting Dean work the toy at his own pace instead of pushing into it. And Dean knows he's coming, feels Castiel tense under him, feels his thighs shake and hears his breath rush out in a silent scream.

And the moment Castiel goes slack in his arms, Dean lets him fall, toy still lodged firmly in his ass. But at least Dean has the brain capacity to turn it off before taking himself in hand. Three strokes, that's all it takes, because just as he touches himself, Cas reaches back and opens himself up, presenting his well-used hole for Dean's viewing pleasure. For Dean to come on. And Dean does. Explosively. Not a thought in his head about condoms, just like every time he's with Castiel.

And once he's wrung out every drop, Cas sighs happily, and his fingers drift down to play around the toy, rubbing Dean's emissions into the tender skin still gripping the pink plastic.

Dean slumps, worn out and completely spent, but his eyes stay fastened to the picture of Cas playing in his come. It's dirty. Fucking filthy the way he swirls it around, the way he pushes it into himself once the vibrator slips out. Dean loves it. Wants to lick it away, make Cas come again, on his tongue. But he knows neither of them is up for that and he isn't sure if it would be welcome. And Cas' time is almost up.

Dean could stay, has before when he doesn't have other appointments. But usually only if Cas still hasn't come. If Dean has played with him too much and not given him the push he needs. And really, in that case, Dean should stay. He can't leave a client unsatisfied. But like this? No. He needs to get out. As soon as possible.

So, naturally, he spends the next fifteen minutes cleaning and putting away the toys and lube (second drawer on the nightstand), cleaning Castiel and himself with a warm wash cloth (cabinet over the sink), helping Castiel out of the jock strap and into a fresh pair of underwear (top dresser drawer), and then covering him with his favorite blanket (the one from the couch because it's soft and perfect Cas size). And it doesn't even occur to him that he goes through this routine on auto pilot now, aware of where everything is and where everything goes.

He stands in the doorway of Castiel's bedroom for a moment, just watching the older man breathe. And god, he's so fucking beautiful that it hurts Dean. In the best way possible. And then he leaves, before he can do or say anything stupid, locking the door behind him.

He thinks they've avoided any awkwardness born of their so out of the norm afternoon together, but then his phone vibrates. Just another rule Dean has broken for Castiel (use condoms, no house calls, don't give out private number or address, and absolutely, no matter what, _do not_ fall in love).

The text message is simple. But Dean's heart almost stops at the implications.

_Dinner? Tomorrow night. I'll cook. You bring wine._

Tomorrow is… not Wednesday. Not a week away. 

Dean doesn't even think about it, doesn't consider clients or appointments. Still standing on the sidewalk in front of Castiel's house, he replies.

_It's a date._

The text he gets in return has him smiling the rest of the day.

_Good :)_

**Author's Note:**

> There's a possibility for a sequel. But I haven't really made up my mind yet. So we'll see.


End file.
